Applications

N,O-Bis(trimethylsilyl)acetamide is used as a regioselective desulfation reagent as well as a preparatory agent for carbohydrate and alcohol trimethylsilyl ethers. It is also used for the derivatization of polar functional groups such as carboxylic acids, phenols, steroids, amines, alcohols, alkaloids and amides. It is employed in the formation of stable trimethylsilyl derivatives. Further, it is used in analytical chemistry for the derivatization of compounds in analysis to increase their volatility and to introduce the trimethylsilyl protecting group in organic synthesis. In addition to this, it is used in the protection of hydroxyl groups in natural products, functional groups in organic intermediates and derivatization reagent for gas chromatography-Mass spectral analysis of phenolic acids in fruits.

Notes

Air and moisture sensitive. Incompatible with strong oxidizing agents, water and acids.

Références bibliographiques

Powerful silylation reagent for a wide range of functional groups under mild conditions. See Appendix 4. Reviews: J. Prakt. Chem./ Chem. Ztg., 337, 332 (1995); Synthesis, 357 (1998). Unlike halosilanes, silylated amides often need no added base catalysts. For an example of use without added solvent or catalyst for the silylation of a tertiary ɑ-hydroxy ketone, see: Org. Synth. Coll., 7, 381 (1990). Silylating power can be increased in polar solvents such as DMF or acetonitrile, or by addition of acidic catalysts, often TMS chloride, or an acid such as TFA or HCl.

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